Every product category has its own iconic items, products that hit it so big that they eventually become rooted in our culture and remain popular for generations, representing the heritage of the brands that started them. The Coca-Cola Bottling Company has Coke (1886). Crayola has its crayons (1903), the British Motor Corporation and its successors developed the Mini (1959) and Nintendo has Mario (1985). Products like these have become such household names because they are instantly recognizable, part of our common language, and we’ve developed an emotional connection to them in our lives.

Clothing is no different. Seasonal updates and fads come and go. Yet, some items have become so deeply embedded in our cultural mindset (and often our wardrobes) that we don’t always realize that they’ve been kicking around for so long and remaining largely unchanged. Very few brands can rely on their iconic products and authentic heritage to sustain strong brand loyalty and respect, especially over time and generations of their customers.

Which leads us to our favorite Five Iconic Pieces of Fashion. Five items from brands with rich heritage that have achieved iconic status, having withstood the passage of time and trends.

Timberland Original Yellow Boot

Though one of the youngest brands on our list, Timberland’s instantly recognizable rugged yellow boots have come a long way in its 40 years, and continue to find new audiences as the brand expanded into different looks and silhouettes. But like all successful brands, Timberland draws from a rich heritage – in this case, the original boot that made it big.

The Brand Behind It

Timberland founder Nathan Swartz started as an apprentice stitcher before buying the Abington Shoe Company, based in Massachusetts in 1955. For the next ten years the Swartz family would produce private label shoes for other manufacturers while developing their injection-molding technology, introduced in the 1960s.

This technology fused soles to leather uppers without the need for stitching, resulting in completely waterproof boots and shoes. It was innovation developed from the utilitarian demands of the rugged New England winters. The Swartz family by then had relocated the company to New Hampshire where they developed the Timberland brand and introduced its first guaranteed waterproof boot under this brand in 1973.

The boots became so popular that the company officially changed its name to The Timberland Company in 1978. Shortly thereafter they introduced hand-sewn shoes and boat shoes, expanding to Europe and Asia, drafting the premium casual lifestyle and rugged authenticity from its iconic boot.

In 2013 the Timberland brand is inspired by the past but newly crafted for today, introducing fresh new styles which are true to their rugged outdoor heritage.

The Icon

The classic wheat-colored boot features a padded leather collar, a full leather lining, and honey lug soles that are permanently bonded to the upper with the injection molding waterproof process. But what really made this boot an icon was the decision to burn its Timberland tree logo into the side of the leather upper, widely discouraged back in 1973 out of fear that damaging the leather in this way would make the boot unsellable. Instead, by the 1980s, guys in New York started wearing the boot and its popularity grew from city to city, coast to coast, creating a cultural movement from the “Al Panino” kids in Milan to the B-style movement in Japan and American hip-hop fashion, which included the yellow boot.

“The boots became so popular that the Swartz’s officially changed the company name from Abington to The Timberland Company in 1978. Shortly thereafter they introduced hand-sewn shoes and boat shoes, expanding to Europe and Asia, drafting the premium casual lifestyle and rugged authenticity from its iconic boot.”

Filson Tin Cloth

Not so much one particular item, but a standard-setting fabric, Filson’s Tin Cloth was named for its impermeability and extreme durability, such that it was likened to one of the toughest metals at the time. The high-grade fabric is used to make a variety of Filson’s products including jackets, vests, bags and outdoor equipment.

The Brand Behind It

Clinton C. Filson had always been brought up with a love of the outdoors and a pioneering spirit thanks to his father. Carrying on this legacy, he opened C.C. Filson’s Pioneer Alaska Clothing and Blanket Manufacturers in 1897, when the Klondike Gold Rush was sending nearly 100,000 prospectors north to the Yukon. Filson first had these customers in mind, designing a variety of Mackinaw (made of heavy wool) goods including clothes and blankets as well as footwear and other items designed for the harsh conditions of the North.

His commitment to quality and reliability would continue long after the Gold Rush ended as he began serving customers working for other industries including loggers, hunters, miners, and explorers. Filson also built his loyal following by constantly communicating with his customers and refining his designs based on their specifications. In fact, if his store didn’t carry something a customer wanted in particular, Filson had it custom-made. His noble commitment to quality can be best summed up by his statement in Filson’s 1914 catalog: “The goods we quote must not be confounded with the cheap and vastly inferior grade with which the market is over-run. Such goods are not only useless for the purpose for which they are intended, but the person wearing them would be better off without them.”

The Icon

Although Filson makes a variety of high-performance fabrics designed for extreme conditions, their most famous is easily their 12.5 oz. Oil Finish Tin Cloth, their heaviest and toughest. The cloth is made by taking a densely-woven 100% cotton canvas fabric and immersing it in a paraffin-based wax, further improving the seal on the already tight weave. Like any pair of prized raw selvedge denim, the fabric starts out extremely stiff. Due to its specially designed finish, the fabric can only be cleaned by wiping and brushing, but gradually softens and develops character through years of use.

“Although Filson makes a variety of high-performance fabrics designed for extreme conditions, their most famous is easily their 12.5 oz. Oil Finish Tin Cloth, their heaviest and toughest. The cloth is made by taking a densely-woven 100% cotton canvas fabric and immersing it in a paraffin-based wax, further improving the seal on the already tight weave.”

Pendleton Fabric

A hundred years since it first started, Pendleton is still renowned for their fabrics and especially their virgin wool blankets. Originating in Pendleton, Oregon, the blankets continue to provide warmth and comfort to those enjoying the wilderness or escaping the cold as they did draped around those at the start of the 20th century.

The Brand Behind It

In 1889, English weaver Thomas Kay opened his own mill in Salem, Oregon after a great many years in the woolen mill industry. He was assisted by his oldest daughter Fannie, who eventually married a retail merchant by the name of C.P. Bishop. Their combined experience was passed down to their sons Clarence, Roy and Chauncey, who would lay the foundation for Pendleton Woolen Mills.

In 1909, the three sons re-started an old mill in Pendleton, Oregon, which first started as a wool scouring plant and produced blankets and robes for Native Americans in 1895 before it became unprofitable and went idle. Under the direction of the brothers Bishop, the mill began to produce Indian blankets again, finding a market with the peoples of the Nez Perce, Navajo, Hopi and Zuni nations as both a piece of apparel and bartering item.

The expansion into other woolen items began in 1912 when Pendleton Woolen Mills opened another weaving mill in Washougal, Washington. Over the years, Pendleton would gradually add new items to its repertoire including men’s virgin wool sportswear and womenswear. Today, five generations later, the Bishop family and Pendleton continue to thrive, overseeing seven facilities and seventy-five retail locations.

The Icon

Pendleton’s fabrics are commonly made out of 100% pure virgin wool, which makes them warm, wrinkle-resistant and easy to care for, and durable. The natural hollow fibers of wool also make them better suited to absorb dyes, resulting in deeper richer colors.

“Pendleton’s fabrics are commonly made out of 100% pure virgin wool, which makes them warm, wrinkle-resistant and easy to care for, and durable. The natural hollow fibers of wool also make them better suited to absorb dyes, resulting in deeper richer colors.”

Hunter Wellington Boots

Whether it was jumping in puddles as a kid or slogging through muddy work conditions, the familiar rubber boots you were wearing probably took their cues from the original design of the innovative Hunter Boots, a nearly 150-year old brand that served the British military throughout both World Wars and the Royal Family.

The Brand Behind It

After the advent of experimenting with materials in shoemaking, including rubber, American entrepreneur Henry Lee Norris and his partner Spencer Thomas Parmelee landed in Scotland searching for a suitable site to produce rubber footwear, starting the North British Rubber Company in 1856. The company began by producing many other products including car tires and had grown to 600 employees in less than twenty years.

The company was first called to action during World War I to produce a total of 1,185,036 pairs of the trench boots for the British Army and a second time during World War II, where yet another large-scale production of rubber footwear was needed for soldiers fighting in the Netherlands.

As the war drew to a close, the boots found popularity in the civilian market where they were the favored choice for keeping feet dry during off weather. They were so well received that after years of supplying to the royal family, the company was issued a Royal Warrant from The Duke of Edinburgh in 1977, and another from The Queen in 1986. the civilian market.

The Icon

Made of vulcanised rubber, the boots are both durable and stylishly moulded so they can pair with different outfits to suit conditions without appearing too clunky. The boots were designed to fulfill a variety of purposes so they also have a comfortable multi-layer sponge insole a quick-drying nylon lining that makes them easy to take off and put on.

“The company was first called to action during World War I to produce a total of 1,185,036 pairs of the trench boots for the British Army and a second time during World War II, where yet another large-scale production of rubber footwear was needed for soldiers fighting in the Netherlands.”

Fred Perry Twin Tipped Shirt

While tennis champion Fred Perry was originally just looking for a new sweatband when he was approached by his future business partner, Tibby Wegner, the ubiquitous polo they came up with quickly became the most recognizable item to carry Perry’s infamous laurel leaf logo.

The Brand Behind It

At the end of the 40’s, Fred Perry was approached by former Austrian footballer Tibby Wegner, who proposed marketing a new sweatband that was lighter and softer than the bath towel gauze Perry was using to catch sweat during his matches. Themselves a first, the sweatbands helped to firmly establish the brand when the two began offering the bands to top players at the best tournaments.

The brand took a huge jump when they began similarly giving their newly designed shirts to not only players such as Hoad and Rosewell, but also BBC cameramen and others, firmly cementing the connection between the Fred Perry logo and the world’s premier tennis tournament, Wimbledon.

Not just limited to the world of tennis, the shirt also found an unexpected fanbase with the then growing Mod movement of the ’60s as its performance-based properties and stylishness allowed the shirt to be worn out for a late night and still be presentable in the morning. This helped the brand make its transition from sportswear to streetwear, where it still enjoys popularity today.

The Icon

There are now lots of tennis shirts out there now, but the Fred Perry original version is kept recognizable with its twin tipping details on the collar and sleeve cuffs, small discreet laurel logo on the chest and seemingly limitless color combinations. They’re made out of 100% cotton piqué, a fabric that has more body and stiffness than your average cotton, making it also more resistant to wrinkling and probably a good reason why the party-hardy Mods took a liking to it.

“Not just limited to the world of tennis, the shirt also found an unexpected fanbase with the then growing Mod movement of the ’60s as its performance-based properties and stylishness allowed the shirt to be worn out for a late night and still be presentable in the morning.”